3-(2-bromoethoxy)benzonitrile | 210963-61-4

• 物质功能分类: 有机原料 - 腈类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(2-bromoethoxy)benzonitrile
• CAS: 210963-61-4
• 化学式: C₉H₈BrNO
• mdl: MFCD09803017
• 分子量: 226.073
• InChiKey: OQAYBNVLPKSUPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-bromoethoxy)benzonitrile 、 4-(4-氨基苯氧基)-1-哌啶甲酸叔丁酯 在 potassium iodide 、 potassium carbonate 作用下， 以 N-甲基乙酰胺 、 乙酸乙酯 为溶剂， 生成 3-[2-[[4-(1-t-butoxycarbonyl-4-piperidyloxy)phenyl]amino]ethoxy]benzonitrile
  参考文献：
  名称：

  BENZAMIDINE DERIVATIVES

  摘要：

  公开号：

  EP0976722B1
• 作为产物：
  描述：

  3-氰基苯酚 、 1,2-二溴乙烷 在 potassium carbonate 、 potassium iodide 作用下， 以 丁酮 为溶剂， 反应 48.0h， 以30%的产率得到3-(2-bromoethoxy)benzonitrile
  参考文献：
  名称：

  New Serotonin 5-HT_1A Receptor Agonists Endowed with Antinociceptive Activity in Vivo

  摘要：

  We report the synthesis of new compounds 4-35 based on two different openings (A and B) of the chromane ring present in the previously identified 5-HT1A receptor (5-HT1AR) ligand 3. The synthesized compounds were assessed for binding affinity, selectivity, and functional activity at the 5-HT1AR Selected candidates resulting from B opening were also evaluated for their potential antinociceptive effect in vivo and pharmacokinetic properties in vitro. Analogue 19 [2-(4-{[2-(2-ethoxyphenoxy)ethyl]amino}butyl)tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione] has been characterized as a high-affinity and potent 5-HT1AR agonist (K-i = 2.3 nM; EC50 = 19 nM). Pharmacokinetic studies indicated that compound 19 displays a good metabolic stability in human liver microsomes (t(1/2) similar to 3 h and CLint = 3.5 mL/min/kg, at 5 mu M), and a low level of protein binding (25%, at 5 mu M). Interestingly, 19 (3 mg/kg, ip, and 30 mg/kg, po) caused significant attenuation of formalin-induced behavior in early and late phases of the mouse intradermal formalin test of pain, and this in vivo effect was reversed by the selective 5-HT1AR antagonist WAY-100635. Thus, the new 5-HT1AR agonist identified in this work, 19, exhibits oral analgesic activity, and the results herein represent a step toward identifying new therapeutics for the control of pain.

  DOI：

  10.1021/jm400766k

文献信息

• Benzamidine derivatives
  申请人：Ajinomoto Co., Inc.

  公开号：US07396844B1

  公开（公告）日：2008-07-08

  Benzamidine derivatives of the following formulae or analogs thereof, i.e., pharmaceutically acceptable salts thereof, are provided. These compounds or salts thereof have a blood-coagulation inhibiting effect based on an excellent effect of inhibiting the action of activated blood coagulation factor X, and they are useful as anticoagulants

  以下化学式或其类似物的苯甲酰胺衍生物，即其药学上可接受的盐，被提供。这些化合物或其盐具有抗血凝作用，基于抑制活化的血凝因子X的作用具有优异的效果，它们可用作抗凝剂。
• US7396844B1
  申请人：——

  公开号：US7396844B1

  公开（公告）日：2008-07-08
• BENZAMIDINE DERIVATIVES
  申请人：Ajinomoto Co., Inc.

  公开号：EP0976722B1

  公开（公告）日：2009-03-11
• New Serotonin 5-HT_1A Receptor Agonists Endowed with Antinociceptive Activity <i>in Vivo</i>
  作者：Margarita Valhondo、Isabel Marco、Mar Martín-Fontecha、Henar Vázquez-Villa、José A. Ramos、Reinhard Berkels、Thomas Lauterbach、Bellinda Benhamú、María L. López-Rodríguez

  DOI：10.1021/jm400766k

  日期：2013.10.24

  We report the synthesis of new compounds 4-35 based on two different openings (A and B) of the chromane ring present in the previously identified 5-HT1A receptor (5-HT1AR) ligand 3. The synthesized compounds were assessed for binding affinity, selectivity, and functional activity at the 5-HT1AR Selected candidates resulting from B opening were also evaluated for their potential antinociceptive effect in vivo and pharmacokinetic properties in vitro. Analogue 19 [2-(4-[2-(2-ethoxyphenoxy)ethyl]amino}butyl)tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione] has been characterized as a high-affinity and potent 5-HT1AR agonist (K-i = 2.3 nM; EC50 = 19 nM). Pharmacokinetic studies indicated that compound 19 displays a good metabolic stability in human liver microsomes (t(1/2) similar to 3 h and CLint = 3.5 mL/min/kg, at 5 mu M), and a low level of protein binding (25%, at 5 mu M). Interestingly, 19 (3 mg/kg, ip, and 30 mg/kg, po) caused significant attenuation of formalin-induced behavior in early and late phases of the mouse intradermal formalin test of pain, and this in vivo effect was reversed by the selective 5-HT1AR antagonist WAY-100635. Thus, the new 5-HT1AR agonist identified in this work, 19, exhibits oral analgesic activity, and the results herein represent a step toward identifying new therapeutics for the control of pain.